KR20110015588A - Ｃ형 간염의 치료를 위한 ７ｈ-인돌로［２，１―ａ］ ［２］ 벤즈아제핀-10-카르복실산 유도체 - Google Patents
Ｃ형 간염의 치료를 위한 ７ｈ-인돌로［２，１―ａ］ ［２］ 벤즈아제핀-10-카르복실산 유도체 Download PDFInfo
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- KR20110015588A KR20110015588A KR1020107027222A KR20107027222A KR20110015588A KR 20110015588 A KR20110015588 A KR 20110015588A KR 1020107027222 A KR1020107027222 A KR 1020107027222A KR 20107027222 A KR20107027222 A KR 20107027222A KR 20110015588 A KR20110015588 A KR 20110015588A
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- Prior art keywords
- alkyl
- mmol
- solvent
- methoxy
- cyclohexyl
- Prior art date
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- 238000011282 treatment Methods 0.000 title abstract description 13
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- 238000000034 method Methods 0.000 claims abstract description 48
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- -1 oxadizolyl Chemical group 0.000 claims description 230
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 184
- 229910052739 hydrogen Inorganic materials 0.000 claims description 182
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 178
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 156
- 125000000217 alkyl group Chemical group 0.000 claims description 131
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 22
- 125000004193 piperazinyl group Chemical group 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
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- 125000002393 azetidinyl group Chemical group 0.000 claims description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 8
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
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- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- UOCLRXFKRLRMKV-UHFFFAOYSA-N trolnitrate phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.[O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O UOCLRXFKRLRMKV-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5074308P | 2008-05-06 | 2008-05-06 | |
| US61/050,743 | 2008-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110015588A true KR20110015588A (ko) | 2011-02-16 |
Family
ID=40786514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107027222A Withdrawn KR20110015588A (ko) | 2008-05-06 | 2009-05-05 | Ｃ형 간염의 치료를 위한 ７ｈ-인돌로［２，１―ａ］ ［２］ 벤즈아제핀-10-카르복실산 유도체 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8133884B2 (enExample) |
| EP (1) | EP2280975B1 (enExample) |
| JP (1) | JP2011520810A (enExample) |
| KR (1) | KR20110015588A (enExample) |
| CN (1) | CN102083834A (enExample) |
| AR (1) | AR071684A1 (enExample) |
| AU (1) | AU2009244409A1 (enExample) |
| BR (1) | BRPI0915130A2 (enExample) |
| CA (1) | CA2723683A1 (enExample) |
| CL (1) | CL2009001089A1 (enExample) |
| CO (1) | CO6290645A2 (enExample) |
| EA (1) | EA201001748A1 (enExample) |
| IL (1) | IL208753A0 (enExample) |
| MX (1) | MX2010011921A (enExample) |
| NZ (1) | NZ588556A (enExample) |
| PE (1) | PE20091879A1 (enExample) |
| TW (1) | TW200951135A (enExample) |
| WO (1) | WO2009137454A1 (enExample) |
| ZA (1) | ZA201007649B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070049593A1 (en) | 2004-02-24 | 2007-03-01 | Japan Tobacco Inc. | Tetracyclic fused heterocyclic compound and use thereof as HCV polymerase inhibitor |
| KR20100124848A (ko) | 2008-03-27 | 2010-11-29 | 브리스톨-마이어스 스큅 컴퍼니 | 방향족 헤테로시클릭 융합된 인돌로벤자디아제핀 ｈｃｖ ｎｓ5ｂ 억제제 |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| WO2013030750A1 (en) | 2011-09-01 | 2013-03-07 | Lupin Limited | Antiviral compounds |
| AU2013217224B2 (en) | 2012-02-10 | 2017-04-06 | Lupin Limited | Antiviral compounds with a dibenzooxaheterocycle moiety |
| US9556204B2 (en) * | 2012-07-18 | 2017-01-31 | Bristol-Myers Squibb Company | Methods and intermediates for the preparation of (4bS,5aR)-12-cyclohexyl-N-(N,N-dimethylsulfamoyl)-3-methoxy-5a-((1R,5S)-3-methyl-3,8-diazabicyclo [3.2.1]octane-8-carbonyl)-4b,5,5a,6-tetrahydrobenzo [3,4]cyclopropa[5,6]azepino[1,2-A]indole-9-carboxamide |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1719773B1 (en) | 2004-02-24 | 2009-04-15 | Japan Tobacco, Inc. | Fused heterotetracyclic compounds and use tehreof as hcv polymerase inhibitor |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| AU2005298412B2 (en) | 2004-10-26 | 2011-06-09 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Tetracyclic indole derivatives as antiviral agents |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7399758B2 (en) | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7473688B2 (en) | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| GB0608928D0 (en) | 2006-05-08 | 2006-06-14 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US7456166B2 (en) | 2006-05-17 | 2008-11-25 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7521441B2 (en) | 2006-05-22 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| ATE469155T1 (de) | 2006-05-25 | 2010-06-15 | Bristol Myers Squibb Co | Cyclopropyl-fusionierte indolbenzazepin-hcv-ns5b- hemmer |
| WO2007140200A2 (en) | 2006-05-25 | 2007-12-06 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
| US7452876B2 (en) | 2006-06-08 | 2008-11-18 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7541351B2 (en) | 2007-01-11 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7517872B2 (en) | 2007-02-22 | 2009-04-14 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7521444B2 (en) | 2007-03-14 | 2009-04-21 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7547690B2 (en) | 2007-03-14 | 2009-06-16 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7538102B2 (en) | 2007-03-14 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US7541353B2 (en) | 2007-03-14 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7538103B2 (en) | 2007-03-15 | 2009-05-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US20090018163A1 (en) | 2007-07-11 | 2009-01-15 | Bristol-Myers Squibb Company | Substituted Heterocyclic Ethers and Their Use in CNS Disorders |
| US7642251B2 (en) | 2007-08-09 | 2010-01-05 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US7652004B2 (en) | 2007-08-09 | 2010-01-26 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8129367B2 (en) | 2007-11-21 | 2012-03-06 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
| US8124601B2 (en) | 2007-11-21 | 2012-02-28 | Bristol-Myers Squibb Company | Compounds for the treatment of Hepatitis C |
-
2009
- 2009-05-04 US US12/434,748 patent/US8133884B2/en active Active
- 2009-05-05 MX MX2010011921A patent/MX2010011921A/es active IP Right Grant
- 2009-05-05 CA CA2723683A patent/CA2723683A1/en not_active Abandoned
- 2009-05-05 BR BRPI0915130A patent/BRPI0915130A2/pt not_active IP Right Cessation
- 2009-05-05 EA EA201001748A patent/EA201001748A1/ru unknown
- 2009-05-05 NZ NZ588556A patent/NZ588556A/en not_active IP Right Cessation
- 2009-05-05 AU AU2009244409A patent/AU2009244409A1/en not_active Abandoned
- 2009-05-05 PE PE2009000605A patent/PE20091879A1/es not_active Application Discontinuation
- 2009-05-05 WO PCT/US2009/042805 patent/WO2009137454A1/en not_active Ceased
- 2009-05-05 KR KR1020107027222A patent/KR20110015588A/ko not_active Withdrawn
- 2009-05-05 CN CN2009801263266A patent/CN102083834A/zh active Pending
- 2009-05-05 JP JP2011508593A patent/JP2011520810A/ja not_active Withdrawn
- 2009-05-05 EP EP09743440.1A patent/EP2280975B1/en not_active Ceased
- 2009-05-06 AR ARP090101641A patent/AR071684A1/es not_active Application Discontinuation
- 2009-05-06 TW TW098115001A patent/TW200951135A/zh unknown
- 2009-05-06 CL CL2009001089A patent/CL2009001089A1/es unknown
-
2010
- 2010-10-14 IL IL208753A patent/IL208753A0/en unknown
- 2010-10-26 ZA ZA2010/07649A patent/ZA201007649B/en unknown
- 2010-10-28 CO CO10134256A patent/CO6290645A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009137454A1 (en) | 2009-11-12 |
| EP2280975A1 (en) | 2011-02-09 |
| NZ588556A (en) | 2012-06-29 |
| CA2723683A1 (en) | 2009-11-12 |
| CL2009001089A1 (es) | 2011-04-29 |
| EA201001748A1 (ru) | 2011-06-30 |
| TW200951135A (en) | 2009-12-16 |
| MX2010011921A (es) | 2010-11-30 |
| JP2011520810A (ja) | 2011-07-21 |
| AR071684A1 (es) | 2010-07-07 |
| EP2280975B1 (en) | 2014-01-01 |
| CN102083834A (zh) | 2011-06-01 |
| AU2009244409A1 (en) | 2009-11-12 |
| PE20091879A1 (es) | 2009-12-19 |
| BRPI0915130A2 (pt) | 2019-09-24 |
| CO6290645A2 (es) | 2011-06-20 |
| ZA201007649B (en) | 2012-04-25 |
| US20090280083A1 (en) | 2009-11-12 |
| US8133884B2 (en) | 2012-03-13 |
| IL208753A0 (en) | 2010-12-30 |
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| PA0105 | International application |
Patent event date: 20101203 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |